Diisopropylethylamine → 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

HRID 394188노트

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HRID 394188 반응식
C(N(C(C)C)CC)(C)C.Br[C:11]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[C:36]([Br:43])[C:12]=1[CH2:13][N:14]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34]C)=[CH:29][CH:28]=1)[C:15]([NH:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])=[O:16]>CN(C=O)C.[Cu]I>[Br:43][C:36]1[CH:37]=[C:38]([N+:40]([O-:42])=[O:41])[CH:39]=[C:11]2[C:12]=1[CH2:13][N:14]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[C:15](=[O:16])[N:17]2[C:18]1[C:19]([Cl:25])=[CH:20][CH:21]=[CH:22][C:23]=1[Cl:24]

참가 물질

5

반응물 2

HCID 81531DiisopropylethylamineHCID 22648032N-(2,6-dibromo-4-nitrobenzyl)-N'-(2,6-dichlorophenyl)-N-(4-ethoxybenzyl)urea

생성물 1

HCID 226481455-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

Diisopropylethylamine (1.78 g, 13.8 mmol) and CuI (2.63 g, 13.8 mmol) was added to N-(2,6-dibromo-4-nitrobenzyl)-N′-(2,6-dichlorophenyl)-N-(4-ethoxybenzyl)urea (4.25 g, 6.88 mmol) in DMF (150 mL). After evacuating and flushing three times with argon, the reaction mixture was heated to 130° C. for 3 h, cooled to rt, and filtered. The filtrate was concentrated under reduced pressure and purified by flash chromatography on Biotage 40M columns, eluting with 80:20 hexanes-acetone to yield 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one. Mass spectrum (ESI) 536.0 (M+1).

후처리

  1. customAfter evacuating
  2. customflushing three times with argon
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography on Biotage 40M columns
  7. washeluting with 80:20 hexanes-acetone

출처 및 근거

ORD 기록
ord-797a6050d93b4dbd846880fffb77b996
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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